Bromobenzene → 1-Benzhydryl-2-benzimidoylazetidine

HRID 46453Notes

Reaction equation

HRID 46453 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=CC=CC=1.[Mg].[CH:17]([N:30]1[CH2:33][CH2:32][CH:31]1[C:34]#[N:35])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[CH:17]([N:30]1[CH2:33][CH2:32][CH:31]1[C:34](=[NH:35])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 5462224MagnesiumHCID 197720721-Benzhydrylazetidine-2-carbonitrileHCID 178418255HCID 178418255, compound

Product 1

HCID 203453011-Benzhydryl-2-benzimidoylazetidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Suspend phenylmagnesium bromide in ether by adding under gentle reflux a solution of 189.2 g of bromobenzene in 500 ml of ether to a stirred suspension of 24.4 g of magnesium turnings in 1000 ml. of dry ether. Upon completion of the addition, reflux for another 30 minutes, then allow the mixture to cool for 15 minutes at room temperature. Add portionwise, over 3 to 4 minutes, 119.6 g of 1-benzhydryl-2-cyanoazetidine. Stir the mixture for 18 hours at room temperature, cool to 0° C. and quench by the sequential addition of 750 ml. of water, 250 ml. of ether and 400 ml. of methylene chloride. Filter the mixture. Remove the aqueous layer of the filtrate. Wash the organic phase with water and dry over anhydrous sodium sulfate. Remove the solvent in vacuo. Triturate the solid residue with 500 ml of isopropyl ether and filter to obtain the analytically pure title product, m.p. 123.5°-126.5° C.

Workup

  1. additionby adding
  2. additionUpon completion of the addition
  3. temperaturereflux for another 30 minutes
  4. additionAdd portionwise, over 3 to 4 minutes
  5. temperaturecool to 0° C.
  6. customquench by the sequential addition of 750 ml
  7. filtrationFilter the mixture
  8. customRemove the aqueous layer of the filtrate
  9. washWash the organic phase with water
  10. dry with materialdry over anhydrous sodium sulfate
  11. customRemove the solvent in vacuo
  12. customTriturate the solid residue with 500 ml of isopropyl ether
  13. filtrationfilter

Sources & evidence

ORD record
ord-201f8ce040b945188807dda424eff77c
Source dataset
uspto-grants-1979_11
Patent number
US04173566

Reaction notes

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